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Modification of carboxylated multiwall nanotubes with benzotriazole derivatives and study of their anticancer activities

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Abstract

In vitro and in vivo results indicate that functionalized carbon nanotubes are promising for the development of unique anticancer drugs. Since therapeutic and pharmacologic agents could functionalize the structure of carbon nanotubes, we report for the first time three-component condensation reactions consisting of multiwalled carbon nanotube–COCl (MWNTCOCl), diazonium sulfonated salt and phenol derivatives to produce novel anticancer agents. The functionalized carboxylated multiwall nanotubes were then characterized by FT-IR, Raman, SEM, TEM, and solubility test. The functionalized MWNTs exhibited good aqueous solubility. Furthermore, the cytotoxic activity of the MWNT–COOH (A) as well as its functionalized carboxylated multiwall nanotubes (MWNT-CO-2-(1-hydroxynaphthalen-2-yl)-2H-benzo[d][1,2,3]triazole-5-sulfonic acid (B), MWNT-CO-2-(2-hydroxy-1-nitrosonaphthalen-3-yl)-2H-benzo[d][1,2,3]triazole-5-sulfonic acid (C) and MWNT-CO-2-(2-hydroxy-5-nitrophenyl)-2H-benzo[d][1,2,3]triazole-5-sulfonic acid (D)) was tested against human gastric cancer MKN45 and human Colon cancer SW742. In vitro cytotoxicity studies represented a significant enhancement in the cytotoxic capability of f-MWNTs, suggesting these drugs improve drug antitumor activity. Therefore, the highly versatile functionalized carboxylated multiwall nanotubes could potentially be considered as anticancer candidates.

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Acknowledgments

The authors like to express their profound gratitude to the Islamic Azad University, Pharmaceutical Sciences Branch, Iran for providing necessary research facilities and financial assistance. The authors also gratefully acknowledge the valuable help of Dr. Hilary Jenkins, research scientist at McMaster University, Canada.

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University, Pharmaceutical Sciences Branch, Tehran, Iran

    Mahdieh Entezari, Mojdeh Safari & Malak Hekmati

  2. Department of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran

    Shohreh Hekmat

  3. Young Researchers Club, Islamic Azad University, Mahshahr Branch, Mahshahr, Iran

    Atena Azin

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  1. Mahdieh Entezari
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  2. Mojdeh Safari
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  3. Malak Hekmati
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  4. Shohreh Hekmat
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Correspondence to Mahdieh Entezari.

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Entezari, M., Safari, M., Hekmati, M. et al. Modification of carboxylated multiwall nanotubes with benzotriazole derivatives and study of their anticancer activities. Med Chem Res 23, 487–495 (2014). https://doi.org/10.1007/s00044-013-0668-3

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